4-(2-Dimethylamino-2-methylpropoxy)-3-fluorobenzaldehyde → (R)-6-{2-{[4-(2-Dimethylamino-2-methylpropoxy)-3-fluorobenzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1434014Notes

Reaction equation

HRID 1434014 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C@@H:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([O:22]C(=O)C(C)(C)C)[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2].[CH3:29][N:30]([CH3:45])[C:31]([CH3:44])([CH3:43])[CH2:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][C:35]=1[F:42]>>[CH3:29][N:30]([CH3:45])[C:31]([CH3:44])([CH3:43])[CH2:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][CH2:2][CH2:1][NH:3][C:4]2[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=2[C@@H:12]2[CH2:21][CH2:20][C:19]3[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15][C:14]=3[CH2:13]2)=[CH:36][C:35]=1[F:42]

Participants

3

Reactant 2

HCID 230871524-(2-Dimethylamino-2-methylpropoxy)-3-fluorobenzaldehydeHCID 57934253HCID 57934253, compound

Product 1

HCID 66627101(R)-6-{2-{[4-(2-Dimethylamino-2-methylpropoxy)-3-fluorobenzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 24.2%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (20 mg) and 4-(2-dimethylamino-2-methylpropoxy)-3-fluorobenzaldehyde (55 mg) according to an analogous synthetic method to Example 264 described below and purified by LC-MS, the title compound (6.6 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-83546f39e0884caaa335c9361ad0821b
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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